JP7012638B2 - Compositions containing taste-regulating compounds, their use and foods containing them - Google Patents

Description

The present invention relates to compositions containing taste-regulating compounds, the use of these compositions, and foods containing them.

The spice industry is constantly looking for ways to enhance, modify or modify the taste of food. One way to do this is to improve the perception of sweetness, flavor, umami, and saltiness; conceal bitterness, acidity, astringency and saltiness; and induce effects such as warming, refreshing or saliva irritation. The addition of a taste-regulating compound that covers a wide range of uses.

Patent Document 1 uses sclareolide to dilute the licorice flavor associated with stevia, whereas Patent Document 2 sweetens with the strength and creaminess of low-fat ice cream and non-nutritive sweeteners such as aspartame. Describes the use of sclareolide to enhance the sensory properties of foods such as the sweetness of attached foods and beverages. However, the use of this compound is limited to such sweeteners.

Patent Document 3 attempts to regulate the flavor and taste with a glucono delta lactone, and this addition is required at a level that results in the associated mild acidity. Patent Document 4 discloses ethylguaiacol and ethylfranelol as saltiness enhancers in soy sauce, and can include the smoke and caramel aroma of these compounds which limit the use of these compounds.

Therefore, there is still a need for flavor-modifying compounds that do not have the above-mentioned drawbacks such as detectable taste or special use and can be used in a wide variety of foods and beverages.

U.S. Patent Application Publication No. 2013/0115356 U.S. Pat. No. 4,917,913 U.S. Pat. No. 5,683,737 Japanese Unexamined Patent Publication No. 2012-070636

S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, N.J., USA

式I
式中
mは0または1であり、
R₃、R₄およびR₇は、独立して水素および直鎖C1～C3アルキル基から選択され、
R₁は、水素、直鎖C1～C3アルキル基および-CH₂OR'から選択され、
R₂およびR₆は、独立して水素、直鎖C1～C3アルキル基もしくは-OR'から選択されるか、またはR₂およびR₆は結合し、直鎖C1～C3アルキル基で任意に置換されるシクロヘキサン環を形成し、
R₅およびR₈は、独立して水素、直鎖C1～C3アルキル基、-CH₂OR'、-CO-R'または-OR'から選択され、
R'は、水素または直鎖C1～C3アルキル基から選択され、
ただし、
C2とC3との間の二重結合が存在する場合、R₅およびR₇は存在せず、
mが1であり、C4とC5との間の二重結合が存在する場合、R₃およびR₁は存在せず、
mが0であり、C2とC3との間の二重結合が存在する場合、R₂およびR₆は結合し、任意に置換されるシクロヘキサン環を形成することを条件とする。 Applicants have found that flavor-modifying compositions comprising a particular flavor-modifying compound can be used to modify the flavor of foods and beverages in a wide range of applications. Accordingly, a first aspect of the invention relates to a flavor-modifying composition comprising one or more flavor-modifying compounds of formula I.

Equation I
During the ceremony
m is 0 or 1 and
R ₃ , R ₄ and R ₇ are independently selected from hydrogen and linear C1-C3 alkyl groups.
R ₁ is selected from hydrogen, linear C1-C3 alkyl groups and -CH ₂ OR'.
R ₂ and R ₆ are independently selected from hydrogen, linear C1-C3 alkyl groups or -OR', or R ₂ and R ₆ are bonded and optionally substituted with linear C1-C3 alkyl groups. Forming a cyclohexane ring
R ₅ and R ₈ are independently selected from hydrogen, linear C1-C3 alkyl groups, -CH ₂ OR', -CO-R' or -OR'.
R'is selected from hydrogen or linear C1-C3 alkyl groups,
However,
If there is a double bond between C2 and C3, then R ₅ and R ₇ are not present,
If m is 1 and there is a double bond between C4 and C5, then R ₃ and R ₁ are not present,
If m is 0 and there is a double bond between C2 and C3, then R ₂ and R ₆ are subject to binding to form an arbitrarily substituted cyclohexane ring.

As used herein, the term "flavor-modifying composition" means that the composition is a natural or synthetic taste substance, flavoring agent, taste profile, flavor profile, and / or texture in an animal or human edible composition. It is intended to mean that the perceptual experience of an edible composition can be modified by enhancing, increasing, enhancing, decreasing, suppressing, or inducing the taste, smell, texture, and / or flavor profile of the profile. ing. The purpose of such modification is primarily to increase the intensity of the desired attribute, to replace the desired attribute that is not present in the edible composition or is lost for some reason, or to reduce the intensity of the undesired attribute. That is. In particular, it is desirable to increase the intensity of saltiness, sweetness, acidity, richness, or umami and suppress the bitterness. The "flavor-modifying composition" provides oral perception provided by chemical sensing of non-basic taste characteristics (called "sensations") including refreshing, pungent (painful), astringent, metallic taste, and salivation in the oral cavity. It can also be enhanced and / modified. In particular, flavor-modifying compositions can reduce astringency and / or stimulate salivary secretion (ie, increased oral water content).

As used herein, the term "flavor-modifying compound" is intended to mean a taste-regulating compound and refers to a molecule that modifies taste and sensory perception (and / or perception). In all cases, the specificity of such compounds is that they do not exhibit perceptible taste and aroma properties (tasteless and aroma-free). Therefore, an important distinguishing feature of these "flavor-modifying compounds" is that while they regulate the flavor perception of foods, they cannot be perceived when taken alone. Such flavor-modifying compounds may be of synthetic or natural origin.

Flavor modifications include increased saltiness, increased sweetness, improved sugar-like quality of high-sweetness sweeteners, reduced bitterness and astringency, stimulation of salivation or increased umami.

According to one embodiment of the invention, the flavor-modifying composition comprises one or more flavor-modifying compounds of formula I in the formula.
m is 0 or 1 and
R ₃ , R ₄ and R ₇ are hydrogen,
R ₁ is selected from hydrogen or linear C1-C3 alkyl groups,
R ₂ and R ₆ are independently selected from hydrogen, linear C1-C3 alkyl groups or -OR'.
R ₅ and R ₈ are independently selected from hydrogen, linear C1-C3 alkyl groups, or -OR'.
R'is selected from hydrogen,
However,
If there is a double bond between C2 and C3, then R ₅ and R ₇ are not present,
If m is 1 and there is a double bond between C4 and C5, then R ₃ and R ₁ are not present,
If m is 0 and there is a double bond between C2 and C3, then R ₂ and R ₆ are subject to binding to form an arbitrarily substituted cyclohexane ring.

According to one embodiment of the invention, the flavor-modifying composition comprises one or more flavor-modifying compounds of formula I in the formula.
m is 0
R ₁ , R ₂ , and R ₇ are hydrogen,
R ₅ and R ₆ are methyl and
R ₈ is a hydroxyl group
There is no double bond between C2 and C3.

According to one embodiment of the invention, the flavor-modifying composition comprises one or more flavor-modifying compounds of formula I in the formula.
m is 1
R ₃ , R ₄ and R ₇ are hydrogen,
R ₁ is selected from hydrogen and methyl groups,
R ₂ and R ₆ are independently selected from hydrogen, methyl group or -OH,
R ₅ and R ₈ are independently selected from hydrogen, linear C1-C3 alkyl groups, or -OH.
However,
If there is a double bond between C2 and C3, then R ₅ and R ₇ are not present and there is no double bond between C 4 and C 5.

According to one embodiment of the invention, the flavor modifying compounds are dihydro-3-hydroxy-4,4-dimethyl-2 (3H) -furanone (pantolactone), 2-acetyl-butyrolactone, 4,6-dimethyl-. Alpha-pyrone, 4-hydroxy-6-methyl-2-pyrone, 3,4-dihydro-6-methyl-2H-pyran-2-one, dihydroactinidiolide, 2-acetyl-2-methyl-gamma-butyrolactone , Dihydro-5- (hydroxymethyl) -2 (3H) -furanone, 3-hydroxy-2-pyrone, D-arabino-1,4-lactone or mixtures thereof.

The flavor-modifying composition comprises a flavor-modifying compound in a food or beverage in an amount of 0.1-200 ppm, preferably 1-100 ppm, more preferably 3-50 ppm, even more preferably 5-20 ppm. Added to food or beverage as present in quantity.

As used herein, the terms "food", "edible composition" and "foodstuff" refer to ingestible products such as, but not limited to, human foods, animal (pet) foods and pharmaceutical compositions. Examples of foodstuffs may include, but are not limited to, snacks, confectionery, plant materials, and meals that may or may not be supplied with essential nutrients. Botanical materials include cocoa, cocoa beans, coffee, coffee beans and tea leaves or powder. Non-limiting examples of foods include salad dressings, sauces, gravy, marinades, rubs, nutrition bars, baked goods, bread, caramel, cooked grains, meat products, poultry products, meat, poultry, chicken, fish, sea protein. Includes sauces, beans, pasta, confectionery products, salty snacks, dairy products, cheese, yogurt, butter, margarine, instant cereals, seasonings and gravy.

Non-limiting examples of animal foods include pet foods, dog foods, cat foods, ferret foods, pocket pet foods, rodent foods, livestock feeds, cattle feeds, goat feeds, etc. Examples include pig feed, sheep feed, horse feed and the like. Pet food, such as dog and cat food, can be made according to the guidelines of the European Pet Food Industry Association (FEDIAF) or the Association of American Feed Control Officials (AAFCO). These guidelines ensure that pet food is perfect and balanced and meets all nutritional requirements of dogs and cats. Other embodiments of pet food can include treats made for dogs and cats. These embodiments may not meet the complete and balanced nutritional requirements specified by FEDIAF and AAFCO.

As used herein, the term "beverage" means a product that is taken orally by a human or animal and supplies the water or other nutrients needed to maintain the health of the human or animal. In particular, the term "beverage" includes, but is not limited to, mixed and concentrated beverages and includes, but is not limited to, alcoholic and non-alcoholic instant beverages and dry powdered beverages. Non-limiting examples of beverages include: soda, carbonated beverages, brewed beverages, dairy products, drinking yogurt, milk, coffee whiteners, nutritional drinks, nutritional beverages, soft carbonated beverages, soft non-carbonated fruit flavors: Beverages, fountain drinks, frozen instant beverages, soft non-carbonated beverages, juices, water, flavored waters, flavored beverages, carbonated waters, syrups, diet beverages, carbonated soft drinks, powdered soft drinks, and liquid concentrates (liquid, frozen) , And those that can be stored at room temperature), fountain syrup, cordial, fruit juice, fruit-containing beverages, fruit-flavored beverages, vegetable juices, vegetable-containing beverages, isotonic beverages, non-isotonic beverages, fruit juice-containing soft drinks, Coffee and coffee-based beverages, substitute coffee, serial-based beverages, tea, tea-containing dry mixed products, and instant tea (herbal tea and tea leaf-based), dairy products, soy products, fruit and vegetable juice and juice-flavored beverages and Juice beverages, juice cocktails, nectar, concentrates, punches, heat (injection, cryosterilization, ultra-high temperature, ohm heating or commercial sterile sterilization) and other beverages processed in hot-filled packaging, filtration, chemical storage, and Low temperature filling products manufactured by other storage techniques. Specific embodiments of carbonated beverages may include, for example, cola, diet cola, lemon lime, orange, orange juice, heavy citrus, fruit flavors, cream soda, tea or tea flavored beverages, and root beer. Certain embodiments of milk can be any suitable form, including non-fat milk, low-fat milk, low-fat milk, whole milk, milk powder or a combination thereof.

In a further embodiment of the invention, the flavor modification composition further comprises a solvent. The solvent not only allows accurate dosage of the flavor-modifying compound to foods and beverages, but also promotes uniform distribution of the flavor-modifying compounds in foods and beverages.

Suitable solvents are hydrophilic solvents such as water, propylene glycol, glycerol, ethanol and triacetin, or vegetable oils such as palm oil, soybean oil, rapeseed oil, sunflower oil, peanut oil, coconut oil, olive oil or medium chain triglyceride (MCT). It may be a hydrophobic solvent such as. Medium chain triglycerides are triglycerides based on aliphatic fatty acids containing 6-12 carbon atoms.

In a further embodiment of the invention, the flavor modification composition further comprises a flavor component.

The terms "flavor component" and "flavor" are compounds recognized by those of skill in the art that can impart or modify the taste of the composition in a positive or pleasing manner, and are simply recognized as compounds having a taste. It is intended to be understood that it is not a compound. Such flavor components can be natural substances, the same substances as natural or artificial substances. In general, these flavor components belong to various chemical classifications such as alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogen or sulfur heterocyclic compounds and essential oils. Many of these co-ingredients are in each case listed in references such as Non-Patent Document 1, or the latest version thereof, or in other studies of similar properties, as well as in the abundant patent literature in the field of flavor. There is.

The compounds of the invention can be readily used to replace all or part of the sugars or sugar substitutes used as sweeteners when used in foods. "Sugar" or "sugar substitute as a sweetener" is any monosaccharide such as fructose , galactose, mannose or glucose, disaccharides such as lactose, sucrose or maltose, starch, oligosaccharides, sugar alcohols, corn syrup. , Polysaccharides such as high fructose corn syrup, "sugar alcohol" sweeteners such as erythritol, isomalt , mannitol , sorbitol, xylitol, martitol, lactitol, maltodextrin, or starch-based, plant-based or seaweed-based (beta) Means the form of other carbohydrates such as glucan, sorbitol) gum. Additional sweeteners include commonly used high-intensity sweeteners, such as aspartame, saccharin, acesulfam-K , sucralose , alitum, hydride starch hydrolyzate (HSH), stebioside, rebaugioside A. , Levagioside B, Levagioside C, Levagioside D, Levagioside F, Levagioside G, Levagioside H and other sweet stevia-based glycosides, Avidia saccharin, Abulsoside, especially Abulsoside A, Abulsoside B, Abulsoside C, Abulsoside D, Aspartame potassium , Albizia saccharin, alitame, aspartame, super aspartame, bayunoside, especially bayunoside 1, bayunoside 2, blazene, brioside, brionoside, brionozzlecoside, carnosifloside, carreram, curculin, cyanine, chlorogenic acid, cyclamate and its salts, cyclocario Sid I, dihydrokercetin-3-acetate, dihydroflavonol, zulcoside, gaudicaugioside, glycyrrhizin, glycyrrhetinic acid, dipenoside, hematoxylin, hernanzulcin, isomogloside, especially isomogloside V, rugsnum, magap, mabinrins, micraclin, mogroside In particular, mogroside IV and mogroside V, monatin and its derivatives, saccharin, mucrodioside, naringindihydrochalcone (NarDHC), neohesperidin dihydrocarcon (NDHC), neotheme, osladin, pentadin, periandrin IV, perilartin, D-phenylalanine, fromisoside, In particular, fromoside 1, fromomisoside 2, fromoside 3, fromomisoside 4, floridin, phyllozlutin, porposioside, polypodoside A, pterocarioside, rubusoside, saccharin and its salts and derivatives, scandenocid, seriguainin A, siamenoside, especially siamenoside I, steviol. Stebioside and other steviol glycosides, strogins, especially strogins 1, strogins 2, strogins 4, suavioside A, suavioside B, suavioside G, suavioside H, suavioside I, suavioside J, sclarose, scuronate, scrooctate, saccharin , Especially somatins I and II, trans-annetol, trans-cinnamaldehyde, trilo Bachin and D-tryptophan, carreram and other guanidine-based sweeteners. Sweeteners also include cyclamic acid, mogroside, tagatose, neotame and other aspartame derivatives, D-tryptophan, glycine, isomalt, and hydrogenated glucose syrup (HGS). The term "sweetener" also includes combinations of sweeteners disclosed herein.

In a further embodiment of the invention, the flavor-modifying composition further comprises one or more additional flavor-modifying compounds that are different from the one or more flavor-modifying compounds of the invention.

In a preferred embodiment of the invention, the flavor modification composition is 5,6-dihydro-4-hydroxy-6-methyl-2H-pyran-2-one, mevalonolactone, 2-methyl-gamma-butyrolactone, 5,6-. Dihydro-2H-pyran-2-one, 3-methyl-2 (5H) -furanone, 5-methoxy-2-pyrrolidinone, hydroxyl-gamma-dodecalactone, massoia lactone, mevanolactone, m-cresol, 3-n-propylphenol , 3-Ethylphenol, 2-Piperidone, 2-Pyrrolidone, Pyrroglutamic acid, 4-Hydroxy-2-pyrrolidinone, N-Methylcaprolactam, Epsilon-Caprolactam and 3-Hydroxy-2-pyrone, 9-Desen-2-one, It further comprises at least one compound selected from the group consisting of mixtures thereof. In a particularly preferred embodiment, dihydro-3-hydroxy-4,4-dimethyl-2 (3H) -furanone (pantolactone) is combined with mevanolactone and / or m-cresol and / or 3-n-propylphenol. used. Without being bound by any theory, it is hypothesized that a synergistic effect will occur between the flavor-modifying compounds (s) of the present invention and the compounds selected from the above group (s). Has been done.

A second aspect of the invention is a product selected from the group of foods and beverages comprising a flavor-modifying composition. In a further embodiment, the product comprises the flavor-modifying compound of the flavor-modifying composition in an amount of 0.1-200 ppm, preferably 1-100 ppm, more preferably 3-50 ppm, even more preferably 5- . Included in an amount of 20 ppm.

A third aspect of the invention is the use of flavor-modifying compositions for modifying the perception of sweetness, saltiness, umami, astringency, salivation and bitterness in foods and beverages.

式I
式中
mは0または1であり、
R₃、R₄およびR₇は、独立して水素および直鎖C1～C3アルキル基から選択され、
R₁は、水素、直鎖C1～C3アルキル基および-CH₂OR'から選択され、
R₂およびR₆は、独立して水素、直鎖C1～C5アルキル基もしくは-OR'から選択されるか、またはR₂およびR₆は結合し、直鎖C1～C3アルキル基で任意に置換されるシクロヘキサン環を形成し、
R₅およびR₈は、独立して水素、直鎖C1～C3アルキル基、-CH₂OR'、-CO-R'または-OR'から選択され、
R'は、水素または直鎖C1～C3アルキル基から選択され、
ただし、
C2とC3との間の二重結合が存在する場合、R₅およびR₇は存在せず、
mが1であり、C4とC5との間の二重結合が存在する場合、R₃およびR₁は存在せず、
mが0であり、C2とC3との間の二重結合が存在する場合、R₂およびR₆は結合し、任意に置換されるシクロヘキサン環を形成することを条件とする。 A fourth aspect of the present invention is a method for improving the perception of sweetness, saltiness, umami, astringency, salivation and bitterness in a food or beverage.
Containing the supply of food or beverage, and the addition of a flavor-modifying composition comprising one or more flavor-modifying compounds of formula I.

Equation I
During the ceremony
m is 0 or 1 and
R ₃ , R ₄ and R ₇ are independently selected from hydrogen and linear C1-C3 alkyl groups.
R ₁ is selected from hydrogen, linear C1-C3 alkyl groups and -CH ₂ OR'.
R ₂ and R ₆ are independently selected from hydrogen, linear C1-C5 alkyl groups or -OR', or R ₂ and R ₆ are bonded and optionally substituted with linear C1-C3 alkyl groups. Forming a cyclohexane ring
R ₅ and R ₈ are independently selected from hydrogen, linear C1-C3 alkyl groups, -CH ₂ OR', -CO-R' or -OR'.
R'is selected from hydrogen or linear C1-C3 alkyl groups,
However,
If there is a double bond between C2 and C3, then R ₅ and R ₇ are not present,
If m is 1 and there is a double bond between C4 and C5, then R ₃ and R ₁ are not present,
If m is 0 and there is a double bond between C2 and C3, then R ₂ and R ₆ are subject to binding to form an arbitrarily substituted cyclohexane ring.

In a first embodiment, the invention provides a method of enhancing saltiness in a food or beverage.

In a second embodiment, the invention provides a method of enhancing sweetness in a food or beverage and / or improving the sugar-like taste perception of a high sweetness sweetener.

In a third embodiment, the invention provides a method of enhancing umami in a food or beverage.

In a fourth embodiment, the invention provides a method of reducing astringency in foods or beverages.

In a fifth embodiment, the invention provides a method of increasing saliva secretion in a food or beverage.

In a further embodiment, the invention provides a method of reducing bitterness in a food or beverage.

The following flavor-modifying compounds were tested in a tabletop screening test: dihydro-3-hydroxy-4,4-dimethyl-2 (3H) -furanone (pantolactone), 2-acetyl-butyrolactone, 4,6-dimethyl-alpha. -Pyrone, 4-hydroxy-6-methyl-2-pyrone, 3,4-dihydro-6-methyl-2H-pyran-2-one, dihydroactinidiolide, 2-acetyl-2-methyl-gamma-butyrolactone, Dihydro-5- (hydroxymethyl) -2 (3H) -furanone, 3-hydroxy-2-pyrone, D-arabino-1,4-lactone. The following taste adjustments were tested: saltiness enhancement, sweetness enhancement, bitterness reduction, umami enhancement.

(Example 1-Effect of cheese sauce on saltiness)
All cheese sauce samples were provided at 21 ° C. Manual agitation was performed before dispensing the sample to ensure a uniform distribution of ingredients. Approximately 9 ml of cheese sauce was placed in an odorless, translucent, 3-digit code-labeled 1 ounce cup and covered. Samples were separated approximately 45 minutes before evaluation.

Panelists evaluated all samples in a fully enclosed compartment booth under white light. Fizz Network Software Acquisitions Biosystemes 2.47B was used for data collection. Each panelist was supplied with filtered water for rinsing and instructed to follow strict rinsing procedures. The rinsing protocol required panelists to rinse before tasting the first sample and after tasting each sample.

Samples were evaluated using the reference deviation (DFR) method. Panelists were given a coded sample at the same time as the identified criteria labeled "000". The encoded sample was either a blind, a coding standard or a coding test sample. The panelists were instructed to first taste the standard (000) and evaluate its saltiness in their hearts. Panelists were instructed to taste the saltiness intensity of the encoded sample and evaluate it against the identified criteria. The sample set was given to the panelists in a balanced and random order. A waiting period of 1 minute was provided between the sample sets to reduce the carry-over of flavor.

Panelists evaluated the difference in saltiness intensity from the criteria using a 9-point scale fixed in the following descriptor: significantly lower than (-4) criteria, same as (0) criteria, more than (4) criteria. Remarkably high. The numbers did not appear in the rating. Statistical mean differences were calculated using one-way ANOVA with Fizz Calculations Biosystemes 2.47B. A significance level p ≤ 0.05 was set for statistical testing.

The modified sample was evaluated to be significantly more salty than the control sample.

(Example 2-in soy sauce)
Maggie Seasoning (Nestle USA, Glendale, CA; Lot # 23261124 15) was supplied as a source of liquid flavored seasonings. Table 2 shows the components and amounts of the sample.

All samples were supplied at 21 ° C. The sample was manually inverted about 5 times before sorting to ensure a uniform distribution of the components. Approximately 6 ml of each sample was placed in an odorless, translucent, 3-digit code-labeled 1 ounce cup and covered. Samples were separated approximately 1 hour before evaluation. Further tests were performed as described in Example 1.

The control was evaluated to be significantly less salty than the variant.

(Example 3-Reduction of sweetness taste threshold value)
Filtered water (Brita® Basic Faucet Filtration System, model # OPFF-100) was collected in a 3.8 L plastic container and added with various concentrations of sucrose, rebaugioside A, or sucralose. A stock solution of each sweetener was prepared, divided in half (by weight) and diluted to obtain the desired concentration level. Then, in a diluted sweetening solution, 0.2% by weight of ethanol (control) or 0.1% of each pantolactone and 5,6-dihydro-4-hydroxy-6-methyl-2H-pyran-2-one (modified) were added. The combination was added. Control and concentrated samples were evaluated twice (twice). Filtered water containing 0.2% ethanol was used as the "blank" sample. Samples were prepared approximately 24 hours before feeding to the panel, divided into odorless translucent plastic cups and covered. All samples were supplied at 21-22 ° C. Four threshold scaling sessions were completed for each sweetener: two sessions of sweeteners containing ethanol (control) and two sessions of sweeteners containing a flavor-modifying composition. Panelists followed the procedure outlined in ASTM Method E679-04.

Panelists received a Trilimb Forced Selection (AFC) sample set consisting of one sweet sample and two blank samples with elevated concentration levels. The panelists were instructed to taste the sample and select a "sweet" sample. Four 3-AFC sets were presented in the session. There was a 1 minute waiting time between the sample sets, during which the panelists were instructed to rinse the taste with filtered water three times. The evaluation was performed in a fully enclosed compartment booth under white light. Data were collected using Fizz Network Software Acquisitions Biosystemes 2.47B.

The results for the individual sweeteners showed low perceptual thresholds for sucrose, Reb-A and sucralose. Overall results showed that when the flavor modification composition was added to the test beverage, sweetness perception was reduced by 53% for sucrose, 34% for levaugioside A, and 35% for sucralose.

Therefore, the pantolactone can be used as a sweetness enhancer, allowing the use of small amounts of sucralose, sucralose and / or rebaugioside A.

(Example 4-Reduction of bitterness and astringency in dark chocolate (86% cocoa) in the presence of pantolactone and mevalonolactone)
In a quantitative descriptive analysis, dark chocolate (Lindt® 85% cocoa) was evaluated with and without (control) and with (test) the above flavor modification compositions (5 ppm pantolactone and 5 ppm mevalonolactone). Twenty-four expert panelists ingested either control dark chocolate or test dark chocolate (30 second delay between sample intakes) in one of the following orders: 1) control first, then test, Or 2) test first, then control. The panel of experts pointed out that when the control was first ingested, the test product tasted: 1) less chocolate, 2) less astringent, and 3) less bitter. In contrast, the panel of experts noted that the test product tasted more chocolate than the control product when the test was first taken. Finally, combining the data from the previous two ratings, the test product was perceived to taste more chocolate. The results confirmed that the order in which the products were evaluated was important when considering the taste of taste-adjusted dark chocolate.

(Example 5-Enhancement of sweetness of barbecue seasoned chips of pantolactone and 5,6-dihydro-4-hydroxy-6-methyl-2H-pyran-2-one)
Three barbecue seasoning chips were evaluated: 1) control-15% seasoning dose, 2) treatment 1-7.5% seasoning dose + 5ppm rebaugioside-A, 3) treatment 2-7.5% seasoning dose + 5ppm rebaugioside- A and pantolactone (5 ppm) and 5,6-dihydro-4-hydroxy-6-methyl-2H-pyran-2-one (5 ppm). Five expert tastings ingested one control barbecue seasoned chip, followed by one chip in treatment 1 and one chip in treatment 2. The results show that a reduced seasoning dose and 5 ppm Reb-A (treatment 1) resulted in a reduced sweetness and a slight bitterness at the end of the flavor profile, while pantolactone and 5,6-dihydro-4-hydroxy-. It was shown that the addition of 6-methyl-2H-pyran-2-one (treatment 2) amplified the refreshing sweetness and torula yeast properties with less bitterness towards the end of the flavor profile.

(Example 6-Various levels of pantolactone (D-isomer) added to cheese sauce enhance saltiness and salivation)
The various concentrations of pantolactone (D-isomer) used in the cheese sauce are shown in Table 6. Five expert tastings ingested the control, followed by samples containing various levels of pantolactone (D-isomer). It was concluded that pantolactone (D-isomer) has a clean taste up to 10-12 ppm in cheese sauce. Above 10-12 ppm, pantolactone increases the bitterness of cheese sauce, but still does not show an offensive odor. In water, pantolactone (D-isomer) with a content of 20-25 ppm is perceived to be slightly unclean, but not unpleasant. Within the sodium fortification, it has a neutral taste.

(Example 7-pantolactone (D-isomer) and mevalonolactone added to chicken broth)
Five expert tastings ingested a control (chicken broth) followed by chicken broth containing either 5 ppm pantolactone (D-isomer) or 5 ppm mevalonolactone. Both pantolactone (D-isomer) and mevalonolactone amplify the umami taste, and the combination of both pantolactone (D-isomer) and mevalonolactone provides a very clean taste improvement without offensive odors. rice field.

(Effect of Pantolactone (D-isomer) on the sweetness of Example 8-rebaugioside-A)
In this example, pantolactone (D-isomer) is added to water containing either 25 ppm or 250 ppm rebaudioside-A (Reb-A) at three concentrations (5, 10, 20 ppm) and a solution. Demonstrated the effect on the sweetness of.

Pantolactone (D-isomer) containing 25 or 250 ppm of Reb-A and no pantolactone (control) added at either 5, 10 or 20 ppm as shown in Table 6. Compare with products containing. Three expert tastings tested the control product followed by the product with increased levels of pantolactone (D-isomer). Increased levels of pantolactone (D-isomer) added to 250 ppm Reb-A aqueous solution resulted in a cleaner, pre-sweetness perception with less aftertaste. After tasting the increased levels of pantolactone (D-isomer) added to 25 ppm Reb-A aqueous solution, the tasting sampler than the control sample until at least 20 ppm of pantolactone (D-isomer) was added. Reported that the sweetness was high.

* PureCircleレバウジオシド-A 97%

* PureCircle Rebaugioside-A 97%

(Example 9-Effect of pantolactone (D-isomer) and mevalonolactone on the pungent taste of chili extract paste)
Pantolactone (D-isomer) and mevalonolactone were added to the chili extract paste at 5 ppm and dissolved in water.

The taste perception of the product without the flavor modification composition (control) was compared with the same product (test) with the flavor modification composition. Four expert tastings took the chili extract paste solution alone and then two dilutions of the chili extract paste solution containing 5 ppm of either pasta lactone (D-isomer) or mevalonolactone (moderate or). I took one of the spicy). When pantolactone (D-isomer) was added to the chili extract paste, the pungent perception was reduced and the pungent aftertaste was reduced. Furthermore, it was concluded that the addition of mevalonolactone to the chili extract paste enhanced the fruitiness but did not change the pungent perception.

(Example 10-Effects of pantolactone (D-isomer) and mevalonolactone on the sweetness and bitterness of milk chocolate)
In this example, pantolactone (D-isomer) and mevalonolactone were added to milk chocolate at 5 ppm each to demonstrate the effect on sweetness and bitterness.

The taste recognition of the product (control) without the addition of the flavor-modified composition was compared with the same product (test) containing the flavor-modified composition. Based on the findings of four expert tastings, it was concluded that the addition of pantolactone (D-isomer) to milk chocolate makes the chocolate sweeter and less bitter.

_{* PureCircle Rebaugioside-A 97%}

(Example 11-Effects of pantolactone (D-isomer), mevalonolactone and mixtures thereof on wine complexity and body).
Pantolactone (D-isomer) and mevalonolactone were added to the wine individually or as a mixture at 5 ppm each. From tests by four expert tastings, it was concluded that pantolactone and mevalonolactone yield wines that are perceived to be more complex and more bodyy, not only in combination, but also alone.

(Example 12-Effect of pantolactone on the flavor balance of tomato-based seasonings)
Ketchup containing sucralose as the base sweetener in the two different formulations and ketchup containing sucralose as the base sweetener in the third formulation without the addition of pantolactone (control) and with the addition of 5.4 ppm. Evaluated in (test). A panel of four experts pointed out that the taste of the first sucrose-based ketchup was improved in a balanced manner, and the sweetness appeared to be slightly suppressed, as evidenced by the increased perception of saltiness. The taste of the second sucrose-based ketchup showed enhanced taste, but not a balanced feel. The taste of sucralose-based ketchup was dramatically improved in all ingredients by the addition of pantolactone (D-isomer), but sucralose needs to be significantly reduced to balance sweetness.

The results confirm that the balanced product enhances the flavor when accompanied by pantolactone (D-isomer).

(Example 13-Pantlactone that enhances saltiness in chicken powder solution)
As shown in Table 12, chicken flour and sodium chloride were added to filtered water (Brita® Basic Faucet Filtration System, model # OPFF-100). The test was performed as shown in Example 1.

There was a significant difference between chicken flour and sodium chloride in aqueous solution and chicken flour and sodium chloride in aqueous solution containing 5 ppm pantolactone when presented on a control basis. When presented with reference to the modified sample, there was no significant difference in saltiness between chicken flour and sodium chloride in aqueous solution and chicken flour and sodium chloride in aqueous solution containing 5 ppm pantolactone.

(Example 14-2-acetyl-butyrolactone and 4-hydroxy-6-methyl-2-pyrone that enhance the saltiness in low-salt soy sauce)
Low-salt soy sauce (Kikkoman®) was evaluated without aqueous solutions of 2-acetyl-butyrolactone and 4-hydroxy-6-methyl-2-pyrone or with a concentration of 5 ppm. Five expert tastings took 1 g of low-salt soy sauce alone, followed by 1 ml of flavor-modifying solution and 1 g of low-salt soy sauce again. The results showed that both 2-acetyl-butyrolactone and 4-hydroxy-6-methyl-2-pyrone amplified the saltiness in low-salt soy sauce (see Table 12).

(Effects of Example 15-2-acetyl-butyrolactone and 4,6-dimethyl-alpha-pyrone on the saltiness of cheese sauce)
Cheese sauce (Ragu®) was evaluated without aqueous solutions of 2-acetyl-butyrolactone and 4,6-dimethyl-alpha-pyrone or with a concentration of 5 ppm. Five expert tastings took 20 g of cheese sauce alone, then 1 ml of flavor-modifying solution, and 20 g of cheese sauce again. The results showed that both 2-acetyl-butyrolactone and 4,6-dimethyl-alpha-pyrone amplified the saltiness in the cheese sauce (see Table 13).

(Effects of Example 16-pantolactone (D-isomer), 2-acetyl-butyrolactone and 4-hydroxy-6-methyl-2-pyrone on the astringency of protein-enriched sports drinks)
In this example, one of pantolactone (D-isomer), 2-acetyl-butyrolactone or 4-hydroxy-6-methyl-2-pyrone is added to the protein-enriched sports drink at 5 ppm each and flavored. The effect of the modified solution on astringency was demonstrated.

The taste recognition of the product without the flavor modification solution (control) is compared with the same product (test) containing the flavor modification solution shown in Table 14. Four expert tastings took the protein-enriched beverage alone, followed by tastings of pantolactone (D-isomer), 2-acetyl-butyrolactone or 4-hydroxy-6-methyl-2-pyrone. A protein-enriched sports drink containing 5 ppm of one of them was ingested and findings were recorded. It was concluded that when all flavor-modifying compounds / solutions were added to protein-enriched sports drinks, they reduced the perception of astringency and the perception of sucralose aftertaste.

(Example 17-Pantlactone, m-cresol and 3-n-propylphenol added to cheese sauce promote saltiness and saliva secretion)
In this example, various embodiments of the pantolactone, m-cresol and 3-n-propylphenol mixture added to the cheese sauce demonstrate enhanced saltiness and salivation.

Many combinations of pantolactone, m-cresol and 3-n-propylphenol are shown in Table 15. Five expert tastings took controls, then each of the treatments, and scored. It was concluded that one of the good blends was a combination of 5.40 ppm pantolactone and 100 ppb m-cresol. 3-n-propylphenol is effective, but exhibits slightly higher levels of flavor and aroma properties.

(Example 18-Desktop screening test)
The following flavor-modifying compounds were tested in a tabletop screening test (alone): dihydro-3-hydroxy-4,4-dimethyl-2 (3H) -furanone (pantolactone), 2-acetyl-butyrolactone, 4,6- Dimethyl-alpha-pyrone, 4-hydroxy-6-methyl-2-pyrone, 3,4-dihydro-6-methyl-2H-pyran-2-one, dihydroactinidiolide, 2-acetyl-2-methyl-gamma -Buchirolactone, dihydro-5- (hydroxymethyl) -2 (3H) -furanone, 3-hydroxy-2-pyrone, D-arabino-1,4-lactone. The following taste adjustments were tested: saltiness enhancement, sweetness enhancement, bitterness reduction, umami enhancement.

Salt taste --Model salt solution-[range of 0.2% to 1.2% salt]
Sodium chloride (NaCl) solution was used as a source for the liquid salt model. The NaCl solution was evaluated without an aqueous solution of the flavor-modifying compound, or typically at a concentration of 5 ppm, but was sometimes tested at 1, 10 and 20 ppm. Up to 5 expert tastings ingested 1 g of NaCl solution alone (control) followed by 1 g of NaCl solution supplemented with 1, 5, 10 or 20 ppm flavor-modifying compound. Attention was paid to the comparison of saltiness intensity, and the saltiness adjustment by the flavor-modifying compound was recorded. At each concentration (1, 5, 10 and 20 ppm flavor-modifying compounds), an increase in saltiness is recorded.

Salty --Maggie (registered trademark) (commercially available, manufactured by Nestle) [10% dilution to the same concentration range]
Maggie® Seasoning (NestleUSA, Glendale, CA) was used as a source of liquid seasonings. Maggie® seasoning solutions were evaluated without an aqueous solution of flavor-modifying compound or typically at a concentration of 5 ppm, but were sometimes tested at 1, 10 and 20 ppm. Up to 5 expert tastings took 1 g of Maggie® alone (control) followed by 1 g of Maggie® with 1, 5, 10 or 20 ppm flavor-modifying compound added. .. Attention was paid to the comparison of saltiness intensity, and the saltiness adjustment by the flavor-modifying compound was recorded. At each concentration (1, 5, 10 and 20 ppm flavor-modifying compounds), an increase in saltiness is recorded.

Salty --Kikkoman soy sauce (normal and low salt) [10% diluted to the same concentration range]
Normal and / or low-salt soy sauce (Kikkoman®) was evaluated without an aqueous solution of the flavor-modifying compound or typically at a concentration of 5 ppm, but sometimes tested at 1, 10 and 20 ppm. went. Up to 5 expert tastings took 1 g of soy sauce alone (control) followed by 1 g of soy sauce with 1, 5, 10 or 20 ppm flavor-modifying compound added. Attention was paid to the comparison of saltiness intensity, and the saltiness adjustment by the flavor-modifying compound was recorded. At each concentration (1, 5, 10 and 20 ppm flavor-modifying compounds), an increase in saltiness is recorded.

Salty-Cheese Sauce Cheese sauce was purchased at a local grocery store. All cheese sauce samples were provided at room temperature (~ 70 ° F). Manual agitation was performed before dispensing the sample to ensure a uniform distribution of ingredients. Approximately 1 ounce of cheese sauce was placed in an odorless, translucent, 1 ounce cup. Up to 5 expert tastings took 5-10 g of cheese sauce alone (control) followed by 5-10 g of cheese sauce with 1, 5, 10 or 20 ppm flavor-modifying compound added. Attention was paid to the comparison of saltiness intensity, and the saltiness adjustment by the flavor-modifying compound was recorded. At each concentration (1, 5, 10 and 20 ppm flavor-modifying compounds), an increase in saltiness is recorded.

Sweetness-Model sucrose solution [range 1.0% to 12.0% sucrose]
Filtered water (Brita® Basic Faucet Filtration System) was used for all diluents. A sucrose solution was made as a source for the liquid sweetness model. Sucrose solutions were evaluated without an aqueous solution of the flavor-modifying compound, or typically at a concentration of 5 ppm, but were sometimes tested at 1, 10 and 20 ppm. Up to 5 expert tastings took 10-20 g of sucrose solution alone (control) followed by 10-20 g of sucrose solution supplemented with 1, 5, 10 or 20 ppm flavor-modifying compound. Attention was paid to the comparison of sweetness intensity, and the sweetness adjustment by the flavor-modifying compound was recorded. At each concentration (1, 5, 10 and 20 ppm flavor-modifying compounds), an increase in sweetness is recorded.

Sweetness-Sucralose solution [range 100ppm-450ppm sucralose]
Filtered water (Brita® Basic Faucet Filtration System) was used for all diluents. A sucralose solution was made as a source for the liquid sweetness model. Sucralose solutions were evaluated without an aqueous solution of flavor-modifying compound, or typically at a concentration of 5 ppm, but were sometimes tested at 1, 10 and 20 ppm. Up to 5 expert tastings took 10-20 g of sucralose solution alone (control) followed by 10-20 g of sucralose solution supplemented with 1, 5, 10 or 20 ppm flavor-modifying compound. Attention was paid to the comparison of sweetness intensity, and the sweetness adjustment by the flavor-modifying compound was recorded. At each concentration (1, 5, 10 and 20 ppm flavor-modifying compounds), an increase in sweetness is recorded.

Sweetness-Reb-A solution [range of 100ppm-450ppm Reb-A]
Filtered water (Brita® Basic Faucet Filtration System) was used for all diluents. Reb-A solution was made as a source of liquid sweetness model. The Reb-A solution was evaluated without an aqueous solution of the flavor-modifying compound, or typically at a concentration of 5 ppm, but was sometimes tested at 1, 10 and 20 ppm. Up to 5 expert tastings can take 10-20 g of Reb-A solution alone (control) followed by 10-20 g of Reb-A solution with 1, 5, 10 or 20 ppm flavor-modifying compound added. Ingested. Attention was paid to the comparison of sweetness intensity, and the sweetness adjustment by the flavor-modifying compound was recorded. At each concentration (1, 5, 10 and 20 ppm flavor-modifying compounds), an increase in sweetness is recorded.

Sweetness --Cork Life (registered trademark) --Commercial product (Coca-Cola product)
Cork Life® (Coca-Cola) was evaluated without an aqueous solution of the flavor-modifying compound, or typically at a concentration of 5 ppm, but was sometimes tested at 1, 10 and 20 ppm. Up to 5 expert tastings 20-30 g of Cork Life® alone (control) followed by 20-30 g of Cork with 1, 5, 10 or 20 ppm flavor-modifying compound added. Ingested Life®. Attention was paid to the comparison of sweetness intensity, and the sweetness adjustment by the flavor-modifying compound was recorded. At each concentration (1, 5, 10 and 20 ppm flavor-modifying compounds), an increase in sweetness is recorded.

Sweetness --Sprite Zero (registered trademark) --Commercial product (Coca-Cola product)
Sprite Zero® (Coca-Cola) was evaluated without an aqueous solution of the flavor-modifying compound, or typically at a concentration of 5 ppm, but was sometimes tested at 1, 10 and 20 ppm. Up to 5 expert tastings 20-30 g of Sprite Zero® alone (control) followed by 20-30 g of Sprite Zero with 1, 5, 10 or 20 ppm flavor-modifying compound added (20-30 g Sprite Zero) Ingested (registered trademark). Attention was paid to the comparison of sweetness intensity, and the sweetness adjustment by the flavor-modifying compound was recorded. At each concentration (1, 5, 10 and 20 ppm flavor-modifying compounds), an increase in sweetness is recorded.

Bitterness-Dark chocolate Dark chocolate (Lindt® 85% cocoa) was melted and used without a flavor-modifying compound (control) or added at a concentration of 5 ppm (test) and used as a sample base. , Sometimes tested at 1, 10 and 20 ppm. Up to 5 expert tastings ingested 10-20 g of chocolate alone (control) followed by 10-20 g of chocolate with 1, 5, 10 or 20 ppm flavor-modifying compound added. Taste regulation by flavor-modifying compounds was recorded, paying attention to the comparison of bitterness, sweetness and salivary secretion intensity. At each concentration (1, 5, 10 and 20 ppm flavor-modifying compounds), record a decrease in bitterness. In addition, record increased sweetness and salivation.

Umami-Maggie (registered trademark) (commercially available, manufactured by Nestle) [10% diluted to the same concentration range]
Maggie® Seasoning (NestleUSA, Glendale, CA) was used as a source of liquid seasonings. Maggie® seasoning solutions were evaluated without an aqueous solution of flavor-modifying compound or typically at a concentration of 5 ppm, but were sometimes tested at 1, 10 and 20 ppm. Up to 5 expert tastings took 1 g of Maggie® alone (control) followed by 1 g of Maggie® with 1, 5, 10 or 20 ppm flavor-modifying compound added. .. Attention was paid to the comparison of saltiness intensity, and the umami adjustment by the flavor-modifying compound was recorded. At each concentration (1, 5, 10 and 20 ppm flavor-modifying compounds), increase umami and saltiness are recorded.

Claims (11)

A product selected from the group of foods and beverages comprising a composition comprising one or more taste-regulating compounds of Formula I.

During the ceremony
m is 0 or 1 and
R ₃ , R ₄ and R ₇ are independently selected from hydrogen and linear C1-C3 alkyl groups.
R ₁ is selected from hydrogen, linear C1-C3 alkyl groups and -CH ₂ OR'.
R ₂ and R ₆ are independently selected from hydrogen, linear C1-C3 alkyl groups or -OR', or R ₂ and R ₆ are bonded and optionally substituted with linear C1-C3 alkyl groups. Form a cyclohexane ring to be
R ₅ and R ₈ are independently selected from hydrogen, linear C1-C3 alkyl groups, -CH ₂ OR', -CO-R' or -OR'.
R'is selected from hydrogen or linear C1-C3 alkyl groups,
However,
If there is a double bond between C2 and C3, then R ₅ and R ₇ are not present,
If m is 1 and there is a double bond between C4 and C5, then R ₃ and R ₁ are not present,
If m is 0 and there is a double bond between C2 and C3, then R ₂ and R ₆ are bound, provided that they form an arbitrarily substituted cyclohexane ring.
Contains one or more of the above taste-regulating compounds in an amount of 0.1-200 ppm
The taste-regulating compound is a product that does not exhibit perceptible taste and aroma properties . The taste-regulating compounds are dihydro-3-hydroxy-4,4-dimethyl-2 (3H) -furanone (pantolactone), 2-acetyl-butyrolactone, 4,6-dimethyl-alpha-pyrone, 4-hydroxy-6. -Methyl-2-pyrone, 3,4-dihydro-6-methyl-2H-pyran-2-one, dihydroactinidiolide, 2-acetyl-2-methyl-gamma-butyrolactone, dihydro-5- (hydroxymethyl) The product according to claim 1 , which is selected from the group consisting of -2 (3H) -furanone, 3-hydroxy-2-pyrone, D-arabino-1,4-lactone or a mixture thereof. The product according to claim 1 or 2 , further comprising a solvent. The product according to any one of claims 1 to 3 , further comprising a flavor component. The product according to any one of claims 1 to 4 , further comprising one or more additional taste-regulating compounds different from those defined in claim 1. 5,6-dihydro-4-hydroxy-6-methyl-2H-pyran-2-one, mevalonolactone, 2-methyl-gamma-butyrolactone, 5,6-dihydro-2H-pyran-2-one, 3-methyl- 2 (5H) -furanone, 5-methoxy-2-pyrrolidinone, hydroxyl-gamma-dodecalactone, massoialactone, m-cresol, 3-n-propylphenol, 3-ethylphenol, 2-piperidone, 2-pyrrolidone, pyrrolidone acid , 4-Hydroxy-2-pyrrolidinone, N-methylcaprolactam, epsilon-caprolactam and 9-decene-2-one, and at least one compound selected from the group consisting of mixtures thereof, further comprising at least one compound selected from the group. The product according to any one of 5 . The product according to claim 1 to 6 , which comprises one or more taste-regulating compounds specified in claims 1 or 2 in an amount of 5 to 20 ppm. The use of a composition to regulate the perception of sweetness, saltiness, umami, astringency, salivation and / or bitterness in foods and beverages .
The composition according to any one of claims 1 to 7 .
The composition is added to the food and beverage so that the amount of the one or more taste-regulating compounds present in the food and beverage is in an amount of 0.1-200 ppm.
The taste-regulating compound does not exhibit perceptible taste and aroma properties , use. To increase the saltiness in the foods and beverages,
To increase the sweetness and / or to improve the sugar-like perception of high-sweetness sweeteners in the foods and beverages.
To increase the umami taste in the foods and beverages,
To reduce the astringency in the foods and beverages,
To increase salivation or to reduce bitterness in said foods and beverages,
The use according to claim 8 . A method of regulating the perception of sweetness, saltiness, umami, astringency, salivation and / or bitterness in foods or beverages.
Supplying food or beverages, and
Including adding the composition according to any one of claims 1 to 7 to the food or beverage.
The composition is added to the food and beverage so that the amount of the one or more taste-regulating compounds present in the food and beverage is in an amount of 0.1-200 ppm.
A method in which the taste-regulating compound exhibits no perceptible taste and aroma properties . To increase the saltiness in the foods and beverages,
To increase the sweetness and / or to improve the sugar-like perception of high-sweetness sweeteners in the foods and beverages.
To increase the umami taste in the foods and beverages,
To reduce the astringency in the foods and beverages,
To increase salivation or to reduce bitterness in said foods and beverages,
The method according to claim 10 .

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